Organic electroluminescent element, compound, and light emitting device, display device and lighting device each using organic electroluminescent element

ABSTRACT

An organic electroluminescent element including a substrate, a pair of electrodes including an anode and a cathode, disposed on the substrate, and at least one organic layer including a light emitting layer, disposed between the electrodes. At least one kind of a compound represented by the following general formula (I) is contained in any layer of the at least one organic layer. The organic electroluminescent element has good luminous efficiency, driving voltage, and driving durability, and has low dependence of such performance on a deposition rate. 
                         
Wherein: L 1  to L 4 , n 1  to n 4 , A 1 , A 5 , A 6 , A 10  and, R are as defined in the application.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a national stage entry of International PatentApplication No. PCT/JP2012/069950, filed 6 Aug. 2012, which in turnclaims priority to, and the benefit of, Japanese Patent Application No.2011-180906, filed 22 Aug. 2011, all of which are incorporated herein byreference in their entireties.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent elementand a compound used therefor (material for an organic electroluminescentelement). The present invention further relates to a light emittingdevice, a display device, or an illumination device, using the organicelectroluminescent element.

BACKGROUND ART

Organic electroluminescent elements (which may hereinafter also bereferred to as “elements” or “organic EL elements”) are light emittingelements which have organic layers between a pair of electrodes, andutilize, for light emitting, energy of the exciton generated as a resultof recombination of electrons injected from a cathode and holes injectedfrom an anode in the organic layer. Since the organic electroluminescentelements are capable of high-luminance light emitting at a low voltage,have a high response speed, and are relatively thin and light-weight, itis expected that the element can be employed in a wide range ofapplications, and the elements have been actively researched anddeveloped. Above all, it is important to develop an organicelectroluminescent element having high luminous efficiency, a lowdriving voltage, and good driving durability in applications withdisplays, and the like, and the results of studies on various researchand development have been reported.

PTL 1 describes that a material in which a ring is formed with a singlebond and a methylene chain with respect to a fused ring structure suchas pyrene can be used as a light emitting material, a host material, orthe like of an organic electroluminescent element. PTL 1 exemplifiesseveral compounds in which aryl pyrene is fused with a pyrene skeletonvia a methylene chain and describes an aspect in which 2 fused rings areformed with the pyrene skeleton and the aryl substituent per pyreneskeleton. However, in Examples of PTL 1, only an investigation on acompound in which 1-aryl pyrene is fused with a pyrene skeleton via amethylene chain has been conducted.

PTL 2 describes that a compound having an aromatic fused hydrocarbonring having 5 to 60 carbon atoms or an aromatic fused heterocycle having2 to 60 carbon atoms as a core, in which there are 1 or 2 phenyl groupsper core skeleton, can be used as a light emitting material for anorganic electroluminescent element. In Examples of PTL 2, it isdescribed that a light emitting layer including the light emittingmaterial is formed at a film forming rate of 5 angstroms/s to 30angstroms/s by a vacuum deposition method to prepare an organicelectroluminescent element.

CITATION LIST Patent Literature

[PTL 1] WO2010/012328 A1

[PTL 2] US2008/0100208 A1

SUMMARY OF INVENTION Technical Problem

However, the present inventors have investigated concerning theseproblems, and thus, they have prepared an organic electroluminescentelements using the light emitting materials described in PTLs 1 and 2.In this regard, they have found that when a film forming rate is changedin the formation of a light emitting layer by a vacuum depositionmethod, the variations in the luminous efficiency, the driving voltage,and the driving durability of the obtained organic electroluminescentelements are high and such performance does not reach a level requiredrecently.

It is an object of the present invention by solving the problems toprovide an organic electroluminescent element, which has good luminousefficiency, driving voltage, and driving durability, and has lowdependence of such performance on a deposition rate.

Solution to Problem

Therefore, the present inventors have conducted extensive investigationsfor the purpose of solving the problems as described above. As a result,they have found that the problems can be solved by using a pyrenederivative having a specific structure, thereby providing the presentinvention as described below.

[1] An organic electroluminescent element including a substrate, a pairof electrodes including an anode and a cathode, disposed on thesubstrate, and at least one organic layer including a light emittinglayer, disposed between the electrodes,

in which at least one kind of compound represented by the followinggeneral formula (I) is contained in any layer of the at least oneorganic layer.

(in which L¹, L², L³ and L⁴ each independently represent a linkinggroup. n¹, n², n³ and n⁴ represent 0 or 1, satisfying n¹+n²=1 and,n³+n⁴=1. A¹, A⁵, A⁶ and A¹⁰ each represent a C atom, C—R¹, or an N atom;and when n¹ is 1, A¹ represents a C atom, when n² is 1, A⁵ represents aC atom, when n³ is 1, A⁶ represents a C atom, when n⁴ is 1, A¹⁰represents a C atom, when n¹ is 0, A¹ represents C—R¹ or an N atom, whenn² is 0, A⁵ represents C—R¹ or an N atom, when n³ is 0, A⁶ representsC—R¹ or an N atom, and when n⁴ is 0, A¹⁰ represents C—R¹ or an N atom.A², A³, A⁴, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

[2] In the organic electroluminescent element as described in [1], inthe general formula (I), L¹, L², L³ and L⁴ are preferably eachindependently CR¹²R¹³, NR¹⁴, siR¹⁵R¹⁶ (R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ eachindependently represent a fluorine atom, an alkyl group, an aryl group,or a heteroaryl group), an O atom, or an S atom.

[3] In the organic electroluminescent element as described in [1] or[2], the compound represented by the general formula (I) is preferably acompound represented by the following general formula (II).

(in which L¹ and L³ each independently represent a linking group. A²,A³, A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

[4] In the organic electroluminescent element as described in [3], inthe general formula (II), L¹ and L³ are preferably each independentlyCR¹²R¹³, NR¹⁴, siR¹⁵R¹⁶ (R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independentlyrepresent a fluorine atom, an alkyl group, an aryl group, or aheteroaryl group), an O atom, or an S atom.

[5] In the organic electroluminescent element as described in [3] or[4], in the general formula (II), A², A³, A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ arepreferably each independently C—R¹.

[6] In the organic electroluminescent element as described in [1] or[2], the compound represented by the general formula (I) is preferably acompound represented by the following general formula (III).

(in which L² and L⁴ each independently represent a linking group. A¹,A², A³, A⁴, A⁶, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

[7] In the organic electroluminescent element as described in [6], inthe general formula (III), L² and L⁴ are preferably each independentlyCR¹²R¹³, NR¹⁴, siR¹⁴R¹⁶ (R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independentlyrepresent a fluorine atom, an alkyl group, an aryl group, or aheteroaryl group), an O atom, or an S atom.

[8] In the organic electroluminescent element as described in [6] or[7], in the general formula (III), A¹, A², A³, A⁴, A⁶, A⁷, A⁸ and A⁹ arepreferably each independently C—R¹.

[9] In the organic electroluminescent element as described in any one of[1] to [8], the compound represented by the general formula (I) ispreferably contained in the light emitting layer.

[10] In the organic electroluminescent element as described in any oneof [1] to [9], the compound represented by the general formula (I) ispreferably a light emitting material contained in the light emittinglayer.

[11] In the organic electroluminescent element as described in [10],further including a host material in the light emitting layer.

[12] In the organic electroluminescent element as described in [11], thehost material preferably has an anthracene skeleton.

[13] In the organic electroluminescent element as described in any oneof [1] to [12], in which the organic layer containing the compoundrepresented by the general formula (I) is formed by a vacuum depositionprocess.

[14] A light emitting device using the organic electroluminescentelement as described in any one of [1] to [13].

[15] A display device using the organic electroluminescent element asdescribed in any one of [1] to [13].

[16] An illumination device using the organic electroluminescent elementas described in any one of [1] to [13].

[17] A compound represented by the following general formula (I).

(in which L¹, L², L³ and L⁴ each independently represent a linkinggroup. n¹, n², n³ and n⁴ represent 0 or 1, satisfying n¹+n²=1 and n³n⁴=1. A¹, A⁵, A⁶ and A¹⁰ each represent a C atom, C—R¹ or an N atom; andwhen n¹ is 1, A¹ represents a C atom, when n² is 1, A⁵ represents a Catom, when n³ is 1, A⁶ represents a C atom, when n⁴ is 1, A¹⁰ representsa C atom, when n¹ is 0, A¹ represents C—R¹ or an N atom, when n² is 0,A⁵ represents C—R¹ or an N atom, when n³ is 0, A⁶ represents C—R¹ or anN atom, when n⁴ is 0, A¹⁰ represents C—R¹ or an N atom. A², A³, A⁴, A⁷,A⁸ and A⁹ each independently represent C—R¹ or an N atom. R¹'s eachindependently represent a hydrogen atom or a substituent. R represents asubstituent bonded to the pyrene skeleton and m represents 0 to 6. Whenm is 2 or more, R's, which are present in plural, may be the same as ordifferent from each other, but there is no case where the adjacent R'sare bonded to each other to form a ring.)

Advantageous Effects of Invention

The organic electroluminescent element of the present invention hasadvantageous effects in that it has good luminous efficiency, drivingvoltage, and driving durability, and has low dependence of suchperformance on a deposition rate. Further, when the compound of thepresent invention is used, such an excellent organic electroluminescentelement can be easily prepared.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view showing one example of a configuration of anorganic electroluminescent element according to the present invention.

FIG. 2 is a schematic view showing one example of alight emitting deviceaccording to the present invention.

FIG. 3 is a schematic view showing one example of an illumination deviceaccording to the present invention.

DESCRIPTION OF EMBODIMENTS

Hereinafter, the details of the present invention will be described. Thedescription of the configuration requirements as described below isbased on representative embodiments and specific examples of the presentinvention, but the present invention is not limited to these embodimentsand specific examples. Incidentally, in the present specification, therange expressed with “to” means a range including the numerical valuesbefore and after “to” as the lower limit and the upper limit,respectively.

[Compound Represented by General Formula (I)]

The compound represented by the general formula (I) of the presentinvention can be preferably used as a material for an organicelectroluminescent element. In the organic electroluminescent element ofthe present invention as described later, the organic layer constitutingthe organic electroluminescent element contains the compound representedby the general formula (I).

(in which L¹, L², L³ and L⁴ each independently represent a linkinggroup. n¹, n², n³ and n⁴ represent 0 or 1, satisfying n¹+n²=1 and,n³+n⁴=1. A¹, A⁵, A⁶ and A¹⁰ each represent a C atom, C—R¹, or an N atom;and when n¹ is 1, A¹ represents a C atom, when n² is 1, A⁵ represents aC atom, when n³ is 1, A⁶ represents a C atom, when n⁴ is 1, A¹⁰represents a C atom, when n¹ is 0, A¹ represents C—R¹ or an N atom, whenn² is 0, A⁵ represents C—R¹ or an N atom, when n³ is 0, A⁶ representsC—R¹ or an N atom, and when n⁴ is 0, A¹⁰ represents C—R¹ or an N atom.A², A³, A⁴, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

Not wishing to be restricted to any theory, when the compoundrepresented by the general formula (I) is used as a material for anorganic electroluminescent element, which has good luminous efficiency,driving voltage, and driving durability, and has low dependence of suchperformance on a deposition rate. It has been completely not known inthe related art that a compound having a structure represented by thegeneral formula (I) exhibits such an effect, and the organicelectroluminescent element exhibiting such an effect becomesadvantageous when it is mounted on a display. In particular, the logicalreason why the dependency of the luminous efficiency, the drivingvoltage, and the driving durability on a deposition rate becomes lowerwas unclear and unpredictable. In the case of using the compound of thepresent invention, it is preferable to prepare an organicelectroluminescent element at a film forming rate during vacuumdeposition in the range of 0.1 angstroms/s to 20 angstroms/s; it is morepreferable to prepare an organic electroluminescent element at a filmforming rate during vacuum deposition in the range of 0.5 angstroms/s to10 angstroms/s; and it is particularly preferable to prepare an organicelectroluminescent element at a film forming rate during vacuumdeposition in the range of 1 angstrom/s to 5 angstroms/s.

Hereinbelow, the compound represented by the general formula (I) will bedescribed in detail.

In the present invention, in the description of the general formula (I),the hydrogen atom includes isotopes thereof (deuterium and the like),and the atom additionally constituting the substituent includes isotopesthereof.

In the present invention, when referring to a “substituent”, thesubstituent may be further substituted. For example, when the “alkylgroup” is referred to in the present invention, it includes an alkylgroup substituted with a fluorine atom (for example, a trifluoromethylgroup) and an alkyl group substituted with an aryl group (for example, atriphenylmethyl group), but when “an alkyl group having 1 to 6 carbonatoms” is referred to herein, it represents any of alkyl groups having 1to 6 carbon atoms, including the alkyl groups which are substituted.

In the general formula (I), L¹, L², L³ and L⁴ each independentlyrepresent a linking group. The linking groups represented by L¹, L², L³and L⁴ are not particularly limited, but monatomic linking groups arepreferred. That is, the atom-linking chain length is preferably 1.

The linking groups represented by L¹, L², L³ and L⁴ preferably eachindependently represent a O atom, S atom, CR¹²R¹³, NR¹⁴ or SiR¹⁵R¹⁶(R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represent a fluorineatom, an alkyl group, an aryl group, or a heteroaryl group).

R¹², R¹³, R¹⁵ and R¹⁶ are more preferably each independently any one ofa fluorine atom, a linear, branched, or cyclic alkyl group having 1 to10 carbon atoms; an aryl group having 6 to 14 carbon atoms; and aheteroaryl group having 3 to 20 carbon atoms and containing at least anyone of N, O, and S as a hetero atom; particularly preferably any one ofa linear or branched alkyl group having 1 to 6 carbon atoms; and an arylgroup having 6 to 10 carbon atoms; and more particularly preferably alinear alkyl group having 1 to 3 carbon atoms or a phenyl group.Further, from the viewpoint of easiness of synthesis, it is preferablethat R¹² and R¹³ be the same substituents. Further, from the viewpointof the same, it is also preferable that R¹⁵ and R¹⁶ be the samesubstituents.

R¹², R¹³, R¹⁵ and R¹⁶ may be combined with each other to form a 5- or6-membered ring. The 5- or 6-membered ring thus formed may be anyone ofa cycloalkyl ring, a cycloalkenyl ring, and a heterocycle. Examples ofthe heterocycle include those containing 1 to 3 hetero atoms selectedfrom a group consisting of a nitrogen atom, an oxygen atom, and a sulfuratom as a ring-constituting atom. The 5- or 6-membered ring thus formedmay have a substituent, examples of the substituent at carbon atomsinclude the following Substituent Group A and examples of thesubstituent at nitrogen atoms include the following Substituent Group B.

<<Substituent Group A>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, t-butyl, n-octyl,n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), analkenyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, vinyl, allyl, 2-butenyl, and 3-pentenyl), analkynyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, propargyl and 3-pentynyl), an aryl group(preferably having 6 to 30 carbon atoms, more preferably having 6 to 20carbon atoms, and particularly preferably having 6 to 12 carbon atoms;for example, phenyl, p-methylphenyl, naphthyl, anthranyl), amino group(preferably having 0 to 30 carbon atoms, more preferably having 0 to 20carbon atoms, and particularly preferably having 0 to 10 carbon atoms;for example, amino, methylamino, dimethylamino, diethylamino,dibenzylamino, diphenylamino, and ditolylamino), an alkoxy group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 10 carbon atoms;for example, methoxy, ethoxy, butoxy, and 2-ethylhexyloxy), and aryloxygroup (preferably having 6 to 30 carbon atoms, more preferably having 6to 20 carbon atoms, and particularly preferably having 6 to 12 carbonatoms; for example, phenyloxy, 1-naphthyloxy, and 2-naphthyloxy), aheterocyclic oxy group (preferably having 1 to 30 carbon atoms, morepreferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 12 carbon atoms; for example, pyridyloxy, pyrazyloxy,pyrimidyloxy, and quinolyloxy), an acyl group (preferably having 2 to 30carbon atoms, more preferably having 2 to 20 carbon atoms, andparticularly preferably having 2 to 12 carbon atoms; for example,acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group(preferably having 2 to 30 carbon atoms, more preferably having 2 to 20carbon atoms, and particularly preferably having 2 to 12 carbon atoms;for example, methoxycarbonyl and ethoxycarbonyl), an aryloxycarbonylgroup (preferably having 7 to 30 carbon atoms, more preferably having 7to 20 carbon atoms, and particularly preferably having 7 to 12 carbonatoms; for example, phenyloxycarbonyl), an acyloxy group (preferablyhaving 2 to 30 carbon atoms, more preferably having 2 to 20 carbonatoms, and particularly preferably having 2 to 10 carbon atoms; forexample, acetoxy and benzoyloxy), an acylamino group (preferably having2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, andparticularly preferably having 2 to 10 carbon atoms; for example,acetylamino and benzoylamino), an alkoxycarbonylamino group (preferablyhaving 2 to 30 carbon atoms, more preferably having 2 to 20 carbonatoms, and particularly preferably having 2 to 12 carbon atoms; forexample, methoxycarbonylamino), an aryloxycarbonylamino group(preferably having 7 to 30 carbon atoms, more preferably having 7 to 20carbon atoms, and particularly preferably having 7 to 12 carbon atoms;for example, phenyloxycarbonylamino), a sulfonylamino group (preferablyhaving 1 to 30 carbon atoms, more preferably having 1 to 20 carbonatoms, and particularly preferably having 1 to 12 carbon atoms; forexample, methanesulfonylamino and benzenesulfonylamino), a sulfamoylgroup (preferably having 0 to 30 carbon atoms, more preferably having 0to 20 carbon atoms, and particularly preferably having 0 to 12 carbonatoms; for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, andphenylsulfamoyl), a carbamoyl group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 12 carbon atoms; for example, carbamoyl,methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl), an alkylthiogroup (preferably having 1 to 30 carbon atoms, more preferably having 1to 20 carbon atoms, and particularly preferably having 1 to 12 carbonatoms; for example, methylthio and ethylthio), an arylthio group(preferably having 6 to 30 carbon atoms, more preferably having 6 to 20carbon atoms, and particularly preferably having 6 to 12 carbon atoms;for example, phenylthio), a heterocyclic thio group (preferably having 1to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example,pyridylthio, 2-benzoimizolylthio, 2-benzoxazolylthio, and2-benzothiazolylthio), a sulfonyl group (preferably having 1 to 30carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example, mesyland tosyl), a sulfinyl group (preferably having 1 to 30 carbon atoms,more preferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 12 carbon atoms; for example, methanesulfinyl andbenzenesulfinyl), a ureido group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 12 carbon atoms; for example, ureido,methylureido, and phenylureido), phosphoramide group (preferably having1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example,diethylphosphoramide and phenylphosphoramide), a hydroxy group, amercapto group, a halogen atom (for example, a fluorine atom, a chlorineatom, a bromine atom, and an iodine atom), a cyano group, a sulfo group,a carboxyl group, a nitro group, a hydroxamic group, a sulfino group, ahydrazino group, an imino group, a heterocyclic group (inclusive of anaromatic heterocyclic group, which preferably has 1 to 30 carbon atoms,and more preferably 1 to 12 carbon atoms and in which examples of thehetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, aphosphorus atom, a silicon atom, a selenium atom, and a tellurium atom;and specific examples thereof include pyridyl, pyrazinyl, pyrimidyl,pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl,triazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl,selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino,pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl,a carbazolyl group, an azepinyl group, and a silolyl group), a silylgroup (preferably having 3 to 40 carbon atoms, more preferably having 3to 30 carbon atoms, and particularly preferably having 3 to 24 carbonatoms; for example, trimethylsilyl and triphenylsilyl), a silyloxy group(preferably having 3 to 40 carbon atoms, more preferably having 3 to 30carbon atoms, and particularly preferably having 3 to 24 carbon atoms;for example, trimethylsilyloxy and triphenylsilyloxy), and a phosphorylgroup (for example, a diphenylphosphoryl group and a dimethylphosphorylgroup). These substituents may be further substituted, and examples ofthe additional substituent include the groups selected from theSubstituent Group A as described above. Further, the substituentsubstituted with a substituent may be further substituted, and examplesof the additional substituent include the groups selected from theSubstituent Group A as described above. In addition, the substituentsubstituted with the substituent substituted with a substituent may befurther substituted, and examples of the additional substituent includethe groups selected from the Substituent Group A as described above.

<<Substituent Group B>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, t-butyl, n-octyl,n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), analkenyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, vinyl, allyl, 2-butenyl, and 3-pentenyl), analkynyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, propargyl and 3-pentynyl), an aryl group(preferably having 6 to 30 carbon atoms, more preferably having 6 to 20carbon atoms, and particularly preferably having 6 to 12 carbon atoms;for example, phenyl, p-methylphenyl, naphthyl, and anthranyl), a cyanogroup, and a heterocyclic group (inclusive of an aromatic heterocyclicgroup, which preferably has 1 to 30 carbon atoms, and more preferably 1to 12 carbon atoms and in which examples of the hetero atom include anitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, asilicon atom, a selenium atom, and a tellurium atom; and specificexamples thereof include pyridyl, pyrazinyl, pyrimidyl, pyridazinyl,pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, triazolyl,isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl,tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl,pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, a carbazolylgroup, an azepinyl group, and a silolyl group). These substituents maybe further substituted, and examples of the additional substituentinclude the groups selected from the Substituent Group A as describedabove. Further, the substituent substituted with a substituent may befurther substituted, and examples of the additional substituent includethe groups selected from the Substituent Group A as described above. Inaddition, the substituent substituted with the substituent substitutedwith a substituent may be further substituted, and examples of theadditional substituent include the groups selected from the SubstituentGroup A as described above.

R¹⁴ is preferably an alkyl group, a perfluoroalkyl group, or an arylgroup. R¹⁴ is more preferably any one of a linear, branched, or cyclicalkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 50carbon atoms; and a heteroaryl group having 5 to 20 carbon atoms and atleast one of N, O, and S as a hetero atom. R¹⁴ is more preferably anaryl group having 6 to 14 carbon atoms; or a heteroaryl group having 3to 20 carbon atoms and at least one of N, O, and S as a hetero atom.

R¹⁴ may have an additional substituent, and the substituent is notparticularly limited, but is preferably an alkyl group or an aryl group.The alkyl group as used herein is preferably an unsubstituted linearalkyl group, an unsubstituted branched alkyl group, an unsubstitutedcycloalkyl group, or a perfluoroalkyl group; more preferably a linearalkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms;particularly preferably a methyl group, an ethyl group, an isopropylgroup, a t-butyl group, a t-amyl group, a neopentyl group, or atrifluoromethyl group; and more particularly preferably a methyl group,an ethyl group, an isopropyl group, or a t-butyl group. On the otherhand, the aryl group as used herein is preferably an aryl group having 6to 14 carbon atoms, more preferably an aryl group having 6 to 10 carbonatoms, and particularly preferably a phenyl group.

In the general formula (I), n¹, n², n³ and n⁴ represent 0 or 1,satisfying n¹+n²=1 and n³+n⁴=1. A¹, A⁵, A⁶ and A¹⁰ each represent a Catom, C—R¹ or an N atom; and when n¹ is 1, A¹ is a C atom, when n² is 1,A⁵ represents a C atom, when n³ is 1, A⁶ represents a C atom, when n⁴ is1, A¹⁰ represents a C atom, when n¹ is 0, A¹ represents C—R¹ or an Natom, when n² is 0, A⁵ represents C—R¹ or an N atom, when n³ is 0, A⁶represents C—R¹ or an N atom, and when n⁴ is 0, A¹⁰ represents C—R¹ oran N atom.

In the general formula (I), A², A³, A⁴, A⁷, A⁸ and A⁹ each independentlyrepresent C—R¹ or an N atom.

The number of nitrogen atoms contained in A¹, A², A³, A⁴ and A⁵ ispreferably 0 to 2, more preferably 0 or 1, and particularly preferably0. That is, as a preferred example, a case where four groups out of A¹to A⁵ are C—R¹, one group out of A¹ or A⁵ is a C atom, and the othergroup is C—R¹ may be mentioned. The preferred positions of nitrogenatoms in the case where nitrogen atoms are contained in A¹, A², A³, A⁴and A⁵ are not particularly limited, but it is preferable that nitrogenatoms be not adjacent to each other.

The number of nitrogen atoms contained in A⁶, A⁷, A⁸, A⁹ and A¹⁰ ispreferably 0 to 2, more preferably 0 or 1, and particularly preferably0. That is, as a preferred example, a case where four groups out of A⁶to A¹⁰ are C—R¹, one group out of A⁶ to A¹⁰ is a C atom, and the othergroup is C—R¹ may be mentioned. The preferred positions of nitrogenatoms in the case where nitrogen atoms are contained in A⁶, A⁷, A⁸, A⁹and A¹⁰ are not particularly limited, but it is preferable that nitrogenatoms be not adjacent to each other.

In the compound represented by the general formula (I), it is preferablethat n¹ be 1 and n² be 0, and it is also preferable that n³ be 1 and n⁴be 0.

In the general formula (I), R¹'s in the case where A¹ to A¹⁰ representC—R¹ each independently represent a hydrogen atom or a substituent.Examples of the substituent where R¹ represent a substituent include theSubstituent Group A as described above. Above all, R¹ is preferably asubstituent having any one of a fluorine atom, an alkyl group, a silylgroup, an aryl group, an aryloxy group, a cyano group, and an aminogroup, and specific examples thereof include a fluorine atom, an alkylgroup, a perfluoroalkyl group, a trialkylsilyl group, a phenyl group, aphenoxy group, and a di-substituted amino group.

R¹ more preferably represents a hydrogen atom, an alkyl group, a silylgroup, an aryl group, an aryloxy group, or a di-substituted amino group,particularly preferably a hydrogen atom, an alkyl group, or adi-substituted amino group, and more particularly preferably a hydrogenatom or an alkyl group.

The alkyl group represented by R¹ is preferably an unsubstituted linearalkyl group, an unsubstituted branched alkyl group, an unsubstitutedcycloalkyl group, or a perfluoroalkyl group, more preferably a linearalkyl group having 1 to 6 carbon atoms, a branched alkyl group having 1to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms,particularly preferably a methyl group, an ethyl group, an isopropylgroup, a t-butyl group, a t-amyl group, a neopentyl group, or atrifluoromethyl group, more particularly preferably a methyl group, anethyl group, an isopropyl group, or a t-butyl group, and still moreparticularly preferably a t-butyl group.

The silyl group represented by R¹ is preferably an alkylsilyl group, andmore preferably a trialkylsilyl group.

The substituted or unsubstituted aryl group represented by R¹ ispreferably an aryl group having 6 to 30 carbon atoms, more preferably aphenyl group, a naphthyl group, an anthryl group, a phenanthryl group,or a pyrenyl group, and particularly preferably a phenyl group or anaphthyl group. The di-substituted amino group represented by R¹ ispreferably an N,N-diarylamino group.

In the general formula (I), R represents a substituent bonded to thepyrene skeleton and m represents 0 to 6. When m is 2 or more, R's, whichare present in plural, may be the same as or different from each other,but there is no case where the adjacent R's are bonded to each other toform a ring.

Examples of the substituent represented by R in the general formula (I)include the Substituent Group A as described above.

m in the general formula (I) is preferably 0 to 2.

The compound represented by the general formula (I) is preferably acompound represented by the general formula (II) or (III), and morepreferably a compound represented by the general formula (II).

First, the general formula (II) will be described.

(in which L¹ and L³ each independently represent a linking group. A²,A³, A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

In the general formula (II), the preferred ranges shown by the grouphaving the same name as in the general formula (I) are the same as thepreferred ranges of the group in the general formula (II). Specifically,in the general formula (II), L¹ and L³ are preferably each independentlyCR¹²R¹³, NR¹⁴, SiR¹⁵R¹⁶, an O atom, or an S atom. Further, in thegeneral formula (II), A², A³, A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ are preferablyeach independently C—R¹.

Next, the general formula (III) will be described.

(in which L² and L⁴ each independently represent a linking group. A¹,A², A³, A⁴, A⁶, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an Natom. R¹'s each independently represent a hydrogen atom or asubstituent. R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6. When m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring.)

In the general formula (III), the preferred ranges shown by the grouphaving the same name as in the general formula (I) are the same as thepreferred ranges of the group in the general formula (III).Specifically, in the general formula (III), L² and L⁴ are preferablyeach independently CR¹²R¹³, NR¹⁴, SiR¹⁵R¹⁶, an O atom, or an S atom.Further, in the general formula (II), A¹, A², A³, A⁴, A⁶, A⁷, A⁸ and A⁹are preferably each independently C—R¹.

In addition, in the case where a site linked with L⁴ and a site linkedwith L² in the general formula (III) are taken as the 1-position and the3-position of pyrene skeleton, respectively, R is preferably present atany at least one of the 6-position and the 8-position of the pyreneskeleton, and more preferably at both of the 6-position and the8-position.

The molecular weight of the compound represented by the general formula(I) is preferably 1000 or less, more preferably 900 or less,particularly preferably 850 or less, and still more preferably 800 orless. By reducing the molecular weight, the sublimation temperature canbe lowered, and accordingly, it is possible to prevent the thermaldecomposition of the compound during deposition. Further, the energyrequired for deposition can be reduced by decreasing the depositiontime. Here, since a material having a high sublimation temperature canundergo thermal decomposition during long-term deposition, it isfavorable that the sublimation temperature be not too high from theviewpoint of deposition suitability. The sublimation temperature (whichmeans a temperature which leads to reduction in 10% by mass in thepresent specification) of the compound represented by the generalformula (I) is preferably 300° C., more preferably 285° C. or lower, andstill more preferably 270° C. or lower.

Specific examples of the compound represented by the general formula (I)are shown below, but it should not be construed that the compoundrepresented by the general formula (I) which can be used in the presentinvention is limited to the specific examples.

The compound represented by the general formula (I) can be synthesizedby the method described in US2008/0100208 or a combination of otherknown reactions. Further, for example, it can also synthesized by thefollowing scheme.

After the synthesis, purification is preferably carried out by columnchromatography, recrystallization, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, or the like can beremoved effectively.

[Organic Electroluminescent Element]

The organic electroluminescent element of the present invention includesa substrate, a pair of electrodes including an anode and a cathode,disposed on the substrate, and at least one organic layer including alight emitting layer, disposed between the electrodes, in which thecompound represented by the general formula (I) is contained in anylayer of the at least one organic layer. In the organicelectroluminescent element of the present invention, at least oneorganic layer including the compound represented by the general formula(I) is preferably the light emitting layer.

The configuration of the organic electroluminescent element of thepresent invention is not particularly limited. FIG. 1 shows one exampleof the configuration of the organic electroluminescent element of thepresent invention. The organic electroluminescent element 10 in FIG. 1has an organic layer between a pair of electrodes (an anode 3 and acathode 9) on a substrate 2.

The element configuration of the organic electroluminescent element, thesubstrate, the cathode, and the anode are described in detail in, forexample, JP-A-2008-270736, and the detailed descriptions described inthis publication can be applied to the present invention.

Hereinafter, preferred aspects of the organic electroluminescent elementof the present invention will be described in detail in the order of thesubstrate, the electrodes, the organic layer, a protective layer, asealing enclosure, a driving method, a light emitting wavelength, andapplications.

<Substrate>

The organic electroluminescent element of the present invention has asubstrate.

The substrate used in the present invention is preferably a substratethat does not scatter or decay light emitted from the organic layer. Inthe case of an organic material, those having excellent heat resistance,dimensional stability, solvent resistance, electrical insulatingproperties, and processability are preferred.

<Electrodes>

The organic electroluminescent element of the present invention has apair of electrodes including an anode and a cathode, disposed on thesubstrate.

In view of the properties of the light emitting element, at least oneelectrode of a pair of electrodes, the anode and the cathode, ispreferably transparent or semi-transparent.

(Anode)

The anode may be usually one having a function as an electrode ofsupplying holes into an organic layer, and is not particularly limitedin terms of its shape, structure, size, or the like. Further, dependingon the use and purpose of the light emitting element, the anode can besuitably selected from the known electrode materials. As describedabove, the anode is usually provided as a transparent anode.

(Cathode)

The cathode may be usually one having a function as an electrode ofinjecting electrons to an organic layer, and is not particularly limitedin terms of its shape, structure, size, or the like. Further, dependingon the use and purpose of the light emitting element, the cathode can besuitably selected from the known electrode materials.

<Organic Layer>

The organic electroluminescent element of the present invention has atleast one organic layer including a light emitting layer, disposedbetween the electrodes, in which at least one kind of compoundrepresented by the general formula (I) is contained in at least onelayer of the entire organic layers.

The organic layer is not particularly limited and can be suitablyselected depending on the use and purpose of the organicelectroluminescent element. However, the organic layer is preferablyformed on the transparent electrode or the semi-transparent electrode.In that case, the organic layer is formed on the whole surface or onesurface of the transparent electrode or the semi-transparent electrode.

The shape, the size, the thickness, and the like of the organic layerare not particularly limited and can be suitably selected depending onthe purpose.

Hereinafter, the configuration of the organic layer, the method forforming an organic layer, preferred aspects of the respective layersconstituting the organic layer, and the materials used in the respectivelayers in the organic electroluminescent element of the presentinvention will be described in detail in order.

(Configuration of Organic Layer)

In the organic electroluminescent element of the present invention, theorganic layer includes a light emitting layer. The organic layerpreferably includes a charge transporting layer. The charge transportinglayer refers to a layer in which charges move when voltage is applied tothe organic electroluminescent element. Specifically, examples thereofinclude a hole injecting layer, a hole transporting layer, an electronblocking layer, a light emitting layer, a hole blocking layer, anelectron transporting layer, and an electron injecting layer. When thecharge transporting layer is a hole injecting layer, a hole transportinglayer, an electron blocking layer, or a light emitting layer, an organicelectroluminescent element can be prepared with low cost and highefficiency.

The compound represented by the general formula (I) is contained in atleast one of the organic layers disposed between the electrodes of theorganic electroluminescent element, and preferably contained in thelight emitting layer in the organic layer disposed between theelectrodes.

However, so far as the gist of the present invention is not deviated,the compound represented by the general formula (I) may be contained inan organic layer other than the light emitting layer of the organicelectroluminescent element of the present invention. Examples of theorganic layer other than the light emitting layer, which may contain thecompound represented by the general formula (I), include a holeinjecting layer, a hole transporting layer, an electron transportinglayer, an electron injecting layer, an exciton blocking layer, and acharge blocking layer (a hole blocking layer, an electron blockinglayer, and the like), preferably any one of an exciton blocking layer, acharge blocking layer, an electron transporting layer, and an electroninjecting layer, and more preferably an exciton blocking layer, a chargeblocking layer, or an electron transporting layer.

In the case where the compound represented by the general formula (I) iscontained in the light emitting layer, the compound represented by thegeneral formula (I) is contained, preferably in the amount of 0.1% bymass to 100% by mass, more preferably 1% by mass to 50% by mass, andstill more preferably 2% by mass to 20% by mass, with respect to thetotal mass of the light emitting layer.

In the case where the compound represented by the general formula (I) iscontained in an organic layer other than the light emitting layer, thecompound represented by the general formula (I) is contained in theorganic layer, preferably in the amount of 70% by mass to 100% by mass,more preferably 80% by mass to 100% by mass, and still more preferably90% by mass to 100% by mass, with respect to the total mass of theorganic layers.

(Method for Forming Organic Layer)

The respective organic layers in the organic electroluminescent elementof the present invention can be suitably formed by any of dry filmforming methods such as a deposition method and a sputtering method, andwet type film forming methods (solution coating methods) such as atransfer method, a printing method, a spin coating method, and a barcoating method.

In the organic electroluminescent element of the present invention, itis preferable that the organic layer including the compound representedby the general formula (I) be formed by a vacuum deposition process. Inparticular, the method for preparing the organic electroluminescentelement of the present invention preferably includes a step of preparingan organic electroluminescent element at a film forming rate duringvacuum deposition in the range of 0.1 angstroms/s to 20 angstroms/s,more preferably includes a step of preparing an organicelectroluminescent element at a film forming rate during vacuumdeposition in the range of 0.5 angstroms/s to 10 angstroms/s, andparticularly preferably includes a step of preparing an organicelectroluminescent element at a film forming rate during vacuumdeposition in the range of 1 angstrom/s to 5 angstroms/s.

(Light Emitting Layer)

The light emitting layer is a layer having a function of, uponapplication of an electric field, receiving holes from the anode, thehole injecting layer, or the hole transporting layer, receivingelectrons from the cathode, the electron injecting layer, or theelectron transporting layer, providing a recombination site of the holesand the electrons, and causing light emitting. However, the lightemitting layer in the present invention is not necessarily limited tothe light emitting by such a mechanism.

The light emitting layer in the organic electroluminescent element ofthe present invention may be constituted of only the light emittingmaterial, or may be constituted as a mixed layer of a host material andthe light emitting material. The light emitting material may be made ofa single kind or two or more kinds thereof. The host material ispreferably a charge transporting material. The host material may be madeof a single kind or two or more kinds thereof. Examples thereof includea configuration in which an electron transporting host material and ahole transporting host material are mixed. Further, the light emittinglayer may include a material which does not have charge transportingproperties and does not emit light.

In addition, the light emitting layer may be made of a single layer ormultiple layers of two or more layers. The respective layers may includethe same light emitting material or host material, and may also includea different material in every layer. In the case where a plurality oflight emitting layers are present in plural, the respective lightemitting layers may emit light in a different luminous color from eachother.

The thickness of the light emitting layer is not particularly limited,but it is preferably usually from 2 nm to 500 nm, and above all, fromthe viewpoint of external quantum efficiency, it is more preferably from3 nm to 200 nm, and still more preferably from 5 nm to 100 nm.

In the organic electroluminescent element of the present invention, in amore preferred aspect, the light emitting layer contains the compoundrepresented by the general formula (I), and the compound represented bythe general formula (I) is used as the light emitting material of thelight emitting layer. Here, the host material as referred to in thepresent specification is a compound which chiefly plays a role ininjecting or transporting charges in the light emitting layer and isalso a compound which does not substantially emit light in itself. Asused herein, the statement “which does not substantially emit light”means that the amount of light emission from the compound which does notsubstantially emit light is preferably 5% or less, more preferably 3% orless, and still more preferably 1% or less, with respect to the totalamount of light emission in the entirety of the element. The compoundrepresented by the general formula (I) may be used as a host material ofthe light emitting layer.

(Light Emitting Material)

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (I) is used as the lightemitting material, but in this case, a combination of the compound withlight emitting materials different from the compound represented by thegeneral formula (I) can be used. Further, in the organicelectroluminescent element of the present invention, in the case wherethe compound represented by the general formula (I) is used as a hostmaterial of the light emitting layer or in the case where the compoundrepresented by the general formula (I) is used in an organic layer otherthan the light emitting layer, the light emitting materials differentfrom the compound represented by the general formula (I) are used in thelight emitting layer.

The light emitting material which can be used in the present inventionmay be any one of a phosphorescent light emitting material, afluorescent light emitting material, and the like. Further, the lightemitting layer in the present invention may contain two or more kinds oflight emitting materials in order to improve the color purity or widenthe light emitting wavelength region.

The fluorescent light emitting material and the phosphorescent materialwhich can be used in the organic electroluminescent element of thepresent invention are described in detail in, for example, paragraphNos. [0100] to [0164] of JP-A-2008-270736 and paragraph Nos. [0088] to[0090] of JP-A-2007-266458, the detailed descriptions thereon in thesepublications can be applied to the present invention.

Examples of the phosphorescent light emitting material which can be usedin the present invention include phosphorescent light emitting materialsdescribed in patent documents, for example, U.S. Pat. No. 6,303,238,U.S. Pat. No. 6,097,147, WO00/57676, WO00/70655, WO01/08230, WO01/39234,WO01/41512, WO02/02714, WO02/15645, WO02/44189, WO05/19373,JP-A-2001-247859, JP-A-2002-302671, JP-A-2002-117978, JP-A-2003-133074,JP-A-2002-235076, JP-A-2003-123982, JP-A-2002-170684, EP1211257,JP-A-2002-226495, JP-A-2002-234894, JP-A-2001-247859, JP-A-2001-298470,JP-A-2002-173674, JP-A-2002-203678, JP-A-2002-203679, JP-A-2004-357791,JP-A-2006-256999, JP-A-2007-19462, JP-A-2007-84635, and JP-A-2007-96259.Above all, examples of the light emitting material which is morepreferred include phosphorescent light emitting metal complex compoundssuch as Ir complexes, Pt complexes, Cu complexes, Re complexes, Wcomplexes, Rh complexes, Ru complexes, Pd complexes, Os complexes, Eucomplexes, Tb complexes, Gd complexes, Dy complexes, and Ce complexes,with Ir complexes, Pt complexes, and Re complexes being particularlypreferred. Above all, Ir complexes, Pt complexes, and Re complexes eachincluding at least one coordination mode of a metal-carbon bond, ametal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond arepreferred. Furthermore, from the viewpoints of luminous efficiency,driving durability, and chromaticity, Ir complexes and Pt complexes areparticularly preferred, and Ir complexes are the most preferred.

The kind of the fluorescent light emitting material which can be used inthe present invention is not particularly limited, but examples thereofinclude those other than the compound represented by the general formula(I), for example, benzoxazole, benzimidazole, benzothiazole,styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene,naphthalimide, coumarin, pyrane, perinone, oxadiazole, aldazine,pyralizine, cyclopentadiene, bisstyrylanthracene, quinacridone,pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine,aromatic fused polycyclic compounds (anthracene, phenanthroline, pyrene,perylene, rubrene, pentacene, and the like), a variety of metalcomplexes typified by metal complexes of 8-quinolinol, pyrromethenecomplexes, and rare-earth complexes, polymer compounds such aspolythiophene, polyphenylene, and polyphenylenevinylene, organicsilanes, and derivatives thereof.

In addition, the compound described in [0082] of JP-A-2010-111620 canalso be used as a light emitting material.

The light emitting layer in the organic electroluminescent element ofthe present invention may be constituted with only a light emittingmaterial or may be constituted as a mixed layer of a host material and alight emitting material. The light emitting material may be made of asingle kind or two or more kinds. The host material is preferably acharge transport material. The host material may be made of a singlekind or two or more kinds. Examples thereof include a configuration inwhich an electron-transporting host material and a hole-transportinghost material are mixed. Furthermore, the light emitting layer maycontain a material which does not have charge transporting propertiesand which does not emit light.

In addition, the light emitting layer may be made of a single layer ortwo or more layers. The respective layers may include the same lightemitting materials or host materials, and may also include differentmaterials from each other over layers. In the case where a plurality oflight emitting layers are present, the respective light emitting layersmay emit light in different luminous colors from each other.

(Host Material)

The host material is a compound that usually plays a role in injectingor transporting charges in the light emitting layer and is also acompound which does not substantially emit light in itself. As usedherein, it is meant by the terms “which does not substantially emitlight” that the amount of light emitting from the compound which doesnot substantially emit light is preferably 5% or less, more preferably3% or less, and still more preferably 1% or less of the total amount oflight emitting in the whole of the element.

Examples of the host material which can be used in the organicelectroluminescent element of the present invention include thefollowing compounds, other than compound represented by the generalformula (I):

conductive high-molecular oligomers such as pyrrole, indole, carbazole,azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole,imidazole, thiophene, benzothiophene, dibenzothiophene, furan,benzofuran, dibenzofuran, polyarylalkanes, pyrazoline, pyrazolone,phenylenediamine, arylamines, amino-substituted chalcone,styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatictertiary amine compounds, styrylamine compounds, porphyrin-basedcompounds, fused ring aromatic hydrocarbon compounds (fluorene,naphthalene, phenanthrene, triphenylene, and the like), polysilane-basedcompounds, poly(N-vinylcarbazole), aniline-based copolymers, thiopheneoligomers, and polythiophene, organic silanes, carbon films, pyridine,pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole,oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone,thiopyran dioxide, carbodiimide, fluorenylidenemethane,distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclictetracarboxylic anhydrides such as naphthalene perylene, phthalocyanine,and a variety of metal complexes typified by metal complexes of8-quinolinol derivatives and metal complexes having metalphthalocyanine, benzoxazole, or benzothiazole as a ligand thereof, andderivatives thereof (which may have a substituent or a fused ring). Inaddition, the compounds described in [0081] or [0083] ofJP-A-2010-111620 can also be used.

Above all, carbazole, dibenzothiophene, dibenzofuran, arylamine,aromatic hydrocarbon compounds with fused rings, and metal complexes arepreferred, and aromatic hydrocarbon compounds with fused rings areparticularly preferred since they are stable. As the aromatichydrocarbon compounds with fused rings, naphthalene-based compounds,anthracene-based compounds, phenanthrene-based compounds,triphenylene-based compounds, and pyrene-based compounds are preferred;anthracene-based compounds and pyrene-based compounds are morepreferred; and anthracene-based compounds are particularly preferred. Asthe anthracene-based compounds, those described in [0033] to [0064] ofWO 2010/134350 are particularly preferred, and examples thereof includeCompounds H-1 and H-2 as described later.

The host material that can be used in the light emitting layer in theorganic electroluminescent element of the present invention may be ahost material having hole transporting properties or a host materialhaving electron transporting properties.

In the light emitting layer, the singlet lowest excited energy (S₁energy) in the film state of the host material is preferably higher thanthe S₁ energy of the light emitting material from the viewpoints ofcolor purity, luminous efficiency, and driving durability. The S₁ of thehost material is preferably higher than the S₁ of the light emittingmaterial by 0.1 eV or more, more preferably by 0.2 eV or more, and stillmore preferably by 0.3 eV or more.

When S₁ in the film state of the host material is lower than S₁ of thelight emitting material, the light emitting is lost, and thus, the hostmaterial is required to have higher S₁ than the light emitting material.Further, even in the case where S₁ of the host material is higher thanthe light emitting material, a small difference in the S₁ of the bothleads to partial reverse energy movement from the light emittingmaterial to the host material, which causes reduction in efficiency,color purity, or durability. Therefore, there is a demand for a hostmaterial having a sufficiently high S₁, and high chemical stability andcarrier injecting/transporting properties.

Furthermore, the content of the host compound in the light emittinglayer in the organic electroluminescent element of the present inventionis not particularly limited, but from the viewpoint of luminousefficiency and driving voltage, it is preferably from 15% by mass to 95%by mass, with respect to the total mass of the compounds forming thelight emitting layer. When the light emitting layer includes a pluralityof kinds of host compounds containing the compound represented by thegeneral formula (I), the content of the compound represented by thegeneral formula (I) is preferably from 50% by mass to 99% by mass, withrespect to the total host compounds.

(Other Layers)

The organic electroluminescent element of the present invention mayinclude layers other than the light emitting layer.

Examples of the organic layer other than the light emitting layer whichmay be included in the organic layer include a hole injecting layer, ahole transporting layer, a blocking layer (a hole blocking layer, anexciton blocking layer, and the like), and an electron transportinglayer. Specifically, examples of the layer configuration include thosedescribed below, but it should not be construed that the presentinvention is limited to these configurations.

-   -   Anode/hole transporting layer/light emitting layer/electron        transporting layer/cathode,    -   Anode/hole transporting layer/light emitting layer/blocking        layer/electron transporting layer/cathode,    -   Anode/hole transporting layer/light emitting layer/blocking        layer/electron transporting layer/electron injecting        layer/cathode,    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/blocking layer/electron transporting        layer/cathode,    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/electron transporting layer/electron injecting        layer/cathode,    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/blocking layer/electron transporting        layer/electron injecting layer/cathode,    -   Anode/hole injecting layer/hole transporting layer/blocking        layer/light emitting layer/blocking layer/electron transporting        layer/electron injecting layer/cathode.

The organic electroluminescent element of the present inventionpreferably includes at least one organic layer which is preferablydisposed between the (A) anode and the light emitting layer. Examples ofthe organic layer which is preferably disposed between the (A) anode andthe light emitting layer include an hole injecting layer, a holetransporting layer, and an electron blocking layer from the anode side.

The organic electroluminescent element of the present inventionpreferably includes at least one organic layer which is preferablydisposed between the (B) cathode and the light emitting layer. Examplesof the organic layer which is preferably disposed between the (B)cathode and the light emitting layer include an electron injectinglayer, an electron transporting layer, and a hole blocking layer fromthe cathode side.

Specifically, an example of the preferred aspects of the organicelectroluminescent element of the present invention is the aspect shownin FIG. 1, in which a hole injecting layer 4, a hole transporting layer5, a light emitting layer 6, a hole blocking layer 7, and an electrontransporting layer 8 are laminated in this order as the organic layerfrom the anode 3 side.

Hereinafter, the layers other than the light emitting layer which theorganic electroluminescent element of the present invention may havewill be described.

(A) Organic Layer Preferably Disposed between Anode and Light EmittingLayer:

First, the (A) organic layer preferably disposed between the anode andthe light emitting layer will be described.

(A-1) Hole Injecting Layer and Hole Transporting Layer

The hole injecting layer and the hole transporting layer are layershaving a function of receiving holes from the anode or the anode sideand transporting them to the cathode side.

The light emitting element of the present invention preferably includesat least one organic layer between the light emitting layer and theanode, and the organic layer preferably includes at least one compoundof the compounds represented by the following general formulae (Sa-1),(Sb-1), and (Sc-1).

(in which X represents a substituted or unsubstituted alkylene grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkenylenegroup having 2 to 30 carbon atoms, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroarylene group having 2 to 30 carbon atoms, or asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms.R^(S1), R^(S2), and R^(S3) each independently represent a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms,a substituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, a hydroxy group, a cyano group, or a substituted orunsubstituted amino group. Adjacent R^(S1), R^(S2), and R^(S3) may bebonded to each other to form a saturated carbocycle or an unsaturatedcarbocycle. Ar^(S1) and Ar^(S2) each independently represent asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.)

(in which R^(S4), R^(S5), R^(S6), and R^(S7) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted aryloxygroup having 6 to 30 carbon atoms, a substituted or unsubstitutedheterocycle having 2 to 30 carbon atoms, a substituted or unsubstitutedfused polycyclic group having 5 to 30 carbon atoms, a hydroxy group, acyano group, or a substituted or unsubstituted amino group. AdjacentR^(S4), R^(S5), R^(S6), and R^(S7) may be bonded to each other to form asaturated carbocycle or an unsaturated carbocycle. Ar^(S3) represents asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.)

(in which R^(S8) and R^(S9) each independently represent a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 30 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms, a substituted or unsubstituted heterocyclic group having 2 to 30carbon atoms, or a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms. R^(S10) represents a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocyclic group having 2 to 30 carbon atoms, or asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms. R^(S11) and R^(S12) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to30 carbon atoms, a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms, a hydroxy group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S11) and R^(S12)may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Ar^(S4) represents a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms. Y^(S1)and Y^(S2) each independently represent a substituted or unsubstitutedalkylene group having 1 to 30 carbon atoms, or a substituted orunsubstituted arylene group having 6 to 30 carbon atoms. n and m eachindependently represent an integer of 0 to 5.)

The general formula (Sa-1) will be described.

In the general formula (Sa-1), X represents a substituted orunsubstituted alkylene group having 1 to 30 carbon atoms, a substitutedor unsubstituted alkenylene group having 2 to 30 carbon atoms, asubstituted or unsubstituted arylene group having 6 to 30 carbon atoms,a substituted or unsubstituted heteroarylene group having 2 to 30 carbonatoms, or a substituted or unsubstituted heterocycle having 2 to 30carbon atoms. X is preferably a substituted or unsubstituted arylenegroup having 6 to 30 carbon atoms, more preferably having a substitutedor unsubstituted phenylene, a substituted or unsubstituted biphenylene,and a substituted or unsubstituted naphthylene, and still morepreferably a substituted or unsubstituted biphenylene.

R^(S1), R^(S2), and R^(S3) each independently represent a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms,a substituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, a hydroxy group, a cyano group, or a substituted orunsubstituted amino group. Adjacent R^(S1), R^(S2), and R^(S3) may bebonded to each other to form a saturated carbocycle or an unsaturatedcarbocycle. Examples of the saturated carbocycle or the unsaturatedcarbocycle include naphthalene, azulene, anthracene, fluorene, andphenalene. R^(S1), R^(S2), and R^(S3) are preferably a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, or a cyano group, and more preferably a hydrogen atom.

Ar^(S1) and Ar^(S2) each independently represent a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar^(S1)and Ar^(S2) are preferably a substituted or unsubstituted phenyl group.

Next, the general formula (Sb-1) will be described.

In the general formula (Sb-1), R^(S4), R^(S5), R^(S6) and R^(S7) eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 30 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocycle having 2 to 30 carbon atoms, or a substitutedor unsubstituted fused polycyclic group having 5 to 30 carbon atoms, ahydroxy group, a cyano group, or a substituted or unsubstituted aminogroup. Adjacent R^(S4), R^(S5), R^(S6) and R^(S7) may be bonded to eachother to form a saturated carbocycle or an unsaturated carbocycle.Examples of the saturated carbocycle or the unsaturated carbocycleinclude naphthalene, azulene, anthracene, fluorene, and phenalene.R^(S4), R^(S5), R^(S6) and R^(S7) are preferably a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, or a cyano group, and more preferably a hydrogen atom.

Ar^(S3) represents a substituted or unsubstituted aryl group having 6 to30 carbon atoms, or a substituted or unsubstituted heteroaryl grouphaving 2 to 30 carbon atoms. Ar^(S3) is preferably a substituted orunsubstituted phenyl group.

Next, the general formula (Sc-1) will be described.

In the general formula (Sc-1), R^(S8) and R^(S9) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclicgroup having 2 to 30 carbon atoms, or a substituted or unsubstitutedfused polycyclic group having 5 to 30 carbon atoms. R^(S8) and R^(S9)are preferably a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, or a substituted or unsubstituted aryl group having 6 to30 carbon atoms, and more preferably a methyl group or a phenyl group.R^(S10) is a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocyclic group having 2to 30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms. R^(S10) is preferably a substitutedor unsubstituted aryl group having 6 to 30 carbon atoms, and morepreferably a phenyl group. R^(S11) and R^(S12) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted aryloxygroup having 6 to 30 carbon atoms, a substituted or unsubstitutedheterocycle having 2 to 30 carbon atoms, a substituted or unsubstitutedfused polycyclic group having 5 to 30 carbon atoms, a hydroxy group, acyano group, or a substituted or unsubstituted amino group. AdjacentR^(S11) and R^(S12) may be bonded to each other to form a saturatedcarbocycle or an unsaturated carbocycle. Examples of the saturatedcarbocycle or the unsaturated carbocycle include naphthalene, azulene,anthracene, fluorene, and phenalene. R^(S11) and R^(S12) are preferablya hydrogen atom, a substituted or unsubstituted alkyl group having 1 to30 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 carbon atoms, a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms, or a cyano group, and more preferably ahydrogen atom. Ar^(S4) represents a substituted or unsubstituted arylgroup having 6 to 30 carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 carbon atoms. Y^(S1) and Y^(S2)represent a substituted or unsubstituted alkylene having 1 to 30 carbonatoms, or substituted or unsubstituted arylene having 6 to 30 carbonatoms. Y^(S1) and Y^(S2) are preferably a substituted or unsubstitutedarylene having 6 to 30 carbon atoms, and more preferably a substitutedor unsubstituted phenylene. n is an integer of 0 to 5, preferably 0 to3, more preferably 0 to 2, and still more preferably 0. m is an integerof 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still morepreferably 1.

The general formula (Sa-1) is preferably a compound represented by thefollowing general formula (Sa-2).

(in which R^(S1), R^(S2), and R^(S3) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to30 carbon atoms, a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms, a hydroxy group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S1), R^(S2), andR^(S3) may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Q^(Sa) each independently represent a hydrogenatom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group.)

The general formula (Sa-2) will be described. R^(S1), R^(S2), and R^(S3)have the same definitions as those in the general formula (Sa-1), andtheir preferred ranges are also the same. Each Q^(Sa) independentlyrepresents a hydrogen atom, a cyano group, a fluorine atom, an alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, an aryloxy group having 6 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30carbon atoms, or a substituted or unsubstituted amino group. Q^(Sa) ispreferably a hydrogen atom, a cyano group, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 carbon atoms,more preferably having a hydrogen atom or a substituted or unsubstitutedalkyl group having 1 to 30 carbon atoms, and still more preferably ahydrogen atom.

The general formula (Sb-1) is preferably a compound represented by thefollowing general formula (Sb-2).

(in which R^(S4), R^(S5), R^(S6) and R^(S7) each independently representa hydrogen atom, a substituted or unsubstituted alkyl group having 1 to30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to30 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 carbon atoms, a substituted or unsubstituted aryloxy group having 6to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2to 30 carbon atoms, a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S4), R^(S5),R^(S6) and R^(S7) may be bonded to each other to form a saturatedcarbocycle or an unsaturated carbocycle. Q^(Sb) represents a hydrogenatom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group.)

The general formula (Sb-2) will be described. R^(S4), R^(S5), R^(S6) andR^(S7) have the same definitions as those in the general formula (Sb-1),and their preferred ranges are also the same. Q^(Sa) represents ahydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group. Q^(Sa) is preferably ahydrogen atom, a cyano group, a fluorine atom, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, or a substitutedor unsubstituted aryl group having 6 to 30 carbon atoms, more preferablyhaving a hydrogen atom, or a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, and still more preferably a hydrogen atom.

The general formula (Sc-1) is preferably a compound represented by thefollowing general formula (Sc-2).

(in which R^(S8) and R^(S9) each independently represent a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 30 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 carbonatoms, a substituted or unsubstituted heterocyclic group having 2 to 30carbon atoms, or a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms. R^(S10) represents a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocyclic group having 2 to 30 carbon atoms, or asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms. R^(S11) and R^(S12) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S11) and R^(S12)may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Q^(Sc) represents a hydrogen atom, a cyanogroup, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, anaryloxy group having 6 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocycle having 2 to 30 carbon atoms, or a substitutedor unsubstituted amino group.)

The general formula (Sc-2) will be described. R^(S8), R^(S9), R^(S10),R^(S11) and R^(S12) have the same definitions as those in the generalformula (Sc-1), and their preferred ranges are also the same. Q^(Sc)represents a hydrogen atom, a cyano group, a fluorine atom, an alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, an aryloxy group having 6 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30carbon atoms, or a substituted or unsubstituted amino group. Q^(Sc) ispreferably a hydrogen atom, a cyano group, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 carbon atoms,more preferably having a hydrogen atom, or a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, and still morepreferably a phenyl group.

Specific examples of the compounds represented by the general formulae(Sa-1), (Sb-1), and (Sc-1) include the following ones. However, thepresent invention is not limited to the following specific examples.

The compound represented by the general formula (Sa-1), (Sb-1), or(Sc-1) can be synthesized by the method described in JP-A-2007-318101.After the synthesis, purification is preferably carried out by columnchromatography, recrystallization, reprecipitation, or the like, andthen by sublimation purification. By the sublimation purification,organic impurities can be separated and inorganic salts, residualsolvents, moisture, or the like can be removed effectively.

In the light emitting element of the present invention, the compoundrepresented by the general formula (Sa-1), (Sb-1), or (Sc-1) ispreferably included in the organic layer between the light emittinglayer and the anode, and above all, it is more preferably included inthe layer on the anode side adjacent to the light emitting layer, and itis particularly preferably a hole transporting material included in thehole transporting layer.

The compound represented by the general formula (Sa-1), (Sb-1), or(Sc-1) is preferably contained in the amount of 70% by mass to 100% bymass, and more preferably 85% by mass to 100% by mass, with respect tothe total mass of the organic layer added.

With respect to the hole injecting layer and the hole transportinglayer, copper phthalocyanine and the like used in Examples as describedlater may be used, in addition to those as described above. Further, thedescriptions in paragraph Nos. [0165] to [0167] of JP-A-2008-270736 canalso be applied to the present invention.

The hole injecting layer preferably contains an electron receptivedopant. By incorporating the electron receptive dopant in the holeinjecting layer, there are effects in which, for example, the holeinjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron receptive dopant may be any oforganic materials and inorganic materials as long as it is capable ofwithdrawing electrons from a material to be doped and generating radicalcations, and examples thereof include TCNQ compounds such astetracyanoquinodimethane (TCNQ), tetrafluorotetracyanoquinodimethane(F₄-TCNQ), hexaazatriphenylene compounds such ashexacyanohexaazatriphenylene (HAT-CN), and molybdenum oxide.

The electron receptive dopant in the hole injecting layer is containedin the amount of preferably from 0.01% by mass to 50% by mass, morepreferably from 0.1% by mass to 40% by mass, and still more preferablyfrom 0.2% by mass to 30% by mass, with respect to the total mass of thecompounds forming the hole injecting layer

(A-2) Electron Blocking Layer

The electron blocking layer is a layer having a function of preventingthe electrons, which have been transported from the cathode side to thelight emitting layer, from passing through to the anode side. In thepresent invention, the electron blocking layer can be provided as anorganic layer adjacent to the light emitting layer on the anode side.

As the organic compound constituting the electron blocking layer, forexample, those exemplified above as the hole transporting material canbe used.

The thickness of the electron blocking layer is preferably from 1 nm to500 nm, more preferably from 3 nm to 100 nm, and still more preferablyfrom 5 nm to 50 nm.

The electron blocking layer may have either a single layer structurecomposed of one or two or more kinds of materials selected from theabove-exemplified materials or a multilayer structure composed of aplurality of layers having the same composition or differentcompositions.

The material used in the electron blocking layer preferably has higherS₁ energy than that of the light emitting material from the viewpointsof color purity, luminous efficiency, and driving durability. The S₁ inthe film state of the material used in the electron blocking layer ispreferably higher than the S₁ of the light emitting material by 0.1 eVor more, more preferably by 0.2 eV or more, and still more preferably by0.3 eV or more.

(B) Organic Layer Preferably Disposed Between Cathode and Light EmittingLayer

Next, the (B) organic layer preferably disposed between the cathode andthe light emitting layer will be described.

(B-1) Electron Injecting Layer and Electron Transporting Layer

The electron injecting layer and the electron transporting layer arelayers having a function of receiving electrons from the cathode or thecathode side and transporting them to the anode side. The electroninjecting material and the electron transporting material used in theselayers may be either a low-molecular compound or a high-molecularcompound.

As the electron transporting material, for example, the compoundrepresented by the general formula (I) can be used. As the otherelectron transporting materials, anyone selected from aromatic ringtetracarboxylic acid anhydrides, such as pyridine derivatives, quinolinederivatives, pyrimidine derivatives, pyrazine derivatives, phthalazinederivatives, phenanthroline derivatives, triazine derivatives, triazolederivatives, oxazole derivatives, oxadiazole derivatives, imidazolederivatives, benzimidazole derivatives, imidazopyridine derivatives,fluorenone derivatives, anthraquinodimethane derivatives, anthronederivatives, diphenylquinone derivatives, thiopyranedioxide derivatives,carbodiimide derivatives, fluorenylidenemethane derivatives,distyrylpyrazine derivatives, naphthalene, and perylene; various metalcomplexes typified by metal complexes of phthalocyanine derivatives or8-quinolinol derivatives and metal complexes having metalphthalocyanine, benzoxazole, or benzothiazole as a ligand thereof,organic silane derivatives typified by silole, hydrocarbon compoundswith fused rings, such as naphthalene, anthracene, phenanthrene,triphenylene, and pyrene is preferred, and any one selected frompyridine derivatives, benzimidazole derivatives, imidazopyridinederivatives, metal complexes, and hydrocarbon compounds with fused ringsis more preferred.

From the viewpoint of decreasing the driving voltage, the thickness ofeach of the electron injecting layer and the electron transporting layeris preferably 500 nm or less.

The thickness of the electron transporting layer is preferably from 1 nmto 500 nm, more preferably from 5 nm to 200 nm, and still morepreferably from 10 nm to 100 nm. In addition, the thickness of theelectron injecting layer is preferably from 0.1 nm to 200 nm, morepreferably from 0.2 nm to 100 nm, and still more preferably from 0.5 nmto 50 nm.

The electron injecting layer and the electron transporting layer mayhave either a single layer structure composed of one or two or morekinds of the above-described materials or a multilayer structurecomposed of a plurality of layers having the same composition ordifferent compositions.

The electron injecting layer preferably contains an electron donatingdopant. By incorporating the electron donating dopant in the electroninjecting layer, there are effects that, for example, the electroninjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron donating dopant may be any oneof organic materials and inorganic materials as long as it is capable ofgiving electrons to the material to be doped and generating radicalanions, and examples thereof include dihydroimidazole compounds such astetrathiafulvalene (TTF), tetrathianaphthacene (TTT), andbis-[1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, andcesium.

The electron donating dopant in the electron injecting layer iscontained in the amount of preferably from 0.01% by mass to 50% by mass,more preferably from 0.1% by mass to 40% by mass, and still morepreferably 0.5% by mass to 30% by mass, with respect to the total massof the compounds forming the electron injecting layer.

(B-2) Hole Blocking Layer

The hole blocking layer is a layer having a function of preventingholes, which have been transported from the anode side to the lightemitting layer, from passing through to the cathode side. In the presentinvention, the hole blocking layer can be provided as an organic layeradjacent to the light emitting layer on the cathode side.

In order that the S₁ energy of the organic compound in the film stateconstituting the hole blocking layer prevents the energy movement ofexcitons produced in the light emitting layer, and thus, does not lowerthe luminous efficiency, it is preferably higher than S₁ energy of thelight emitting material.

As an example of the organic compound constituting the hole blockinglayer, for example, the compound represented by the general formula (I)can be used.

Examples of the organic compounds constituting the hole blocking layer,other than the compound represented by the general formula (I), includealuminum complexes such as aluminum (III) bis(2-methyl-8-quinolinato)4-phenylphenolate (abbreviated as Balq), triazole derivatives, andphenanthroline derivatives such as2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP).

The thickness of the hole blocking layer is preferably from 1 nm to 500nm, more preferably from 3 nm to 100 nm, and still more preferably from5 nm to 50 nm.

The hole blocking layer may have either a single layer structurecomposed of one or two or more kinds of the above-described materials ora multilayer structure composed of a plurality of layers having the samecomposition or different compositions.

The material used in the hole blocking layer preferably has higher S₁energy than that of the light emitting material from the viewpoints ofcolor purity, luminous efficiency, and driving durability. The S₁ in thefilm state of the material used in the hole blocking layer is preferablyhigher than the S₁ of the light emitting material by 0.1 eV or more,more preferably by 0.2 eV or more, and still more preferably by 0.3 eVor more.

(B-3) Material which is Particularly Preferably Used in Organic Layer,Preferably Disposed Between Cathode and Light Emitting Layer

For the organic electroluminescent element of the present invention,examples of the material which is particularly preferably used in the(B) materials for an organic layer, preferably disposed between thecathode and the light emitting layer include the compound represented bythe general formula (I), a compound represented by the following generalformula (O-1), and a compound represented by the following generalformula (P).

Hereinafter, a compound represented by the general formula (O-1) and acompound represented by the general formula (P) will be described.

The organic electroluminescent element of the present inventionpreferably includes at least one organic layer between the lightemitting layer and the cathode, and the organic layer preferablycontains at least one of compounds represented by the following generalformula (O-1), from the viewpoint of efficiency or driving voltage of anelement. Hereinafter, the general formula (O-1) will be described.

(In the general formula (O-1), R^(O1) represents an alkyl group, an arylgroup, or a heteroaryl group. A^(O1) to A^(O4) each independentlyrepresent C—R^(A) or a nitrogen atom. R^(A) represents a hydrogen atom,an alkyl group, an aryl group, or a heteroaryl group, and a plurality ofR^(A)'s may be the same as or different from each other. L^(O1)represents any of divalent to hexavalent linking groups with an arylring or a heteroaryl ring. n^(O1) represents an integer of 2 to 6).

R^(O1) represents an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave a substituent selected from the above-described Substituent GroupA. R^(O1) is preferably an aryl group or a heteroaryl group, and morepreferably an aryl group. Preferred examples of the substituent in thecase where the aryl group of R^(O1) has a substituent include an alkylgroup, an aryl group, and a cyano group, more preferably an alkyl groupand an aryl group, and still more preferably an aryl group. In the casewhere the aryl group of R^(O1) has a plurality of substituents, theplurality of substituents may be bonded to each other to form a 5- or6-membered ring. The aryl group of R^(O1) is preferably a phenyl groupwhich may have a substituent selected from Substituent Group A, morepreferably a phenyl group which may be substituted with an alkyl groupor an aryl group, and still more preferably an unsubstituted phenylgroup or 2-phenylphenyl group.

A^(O1) to A^(O4) each independently represent C—R^(A) or a nitrogenatom. It is preferable that 0 to 2 groups out of A^(O1) to A^(O4) benitrogen atoms; and it is more preferable that 0 or 1 group out ofA^(O1) to A^(O4) be nitrogen atoms. It is preferable that all of A^(O1)to A^(O4) be C—R^(A), or A^(O1) be a nitrogen atom, and A^(O2) to A^(O4)are C—R^(A); it is more preferable that A^(O1) be a nitrogen atom, andA^(O2) to A^(O4) be C—R^(A); it is still more preferable that A^(O1) bea nitrogen atom, A^(O2) to A^(O4) be C—R^(A), and R^(A)'s be allhydrogen atoms.

R^(A) represents a hydrogen atom, an alkyl group (preferably having 1 to8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms),or a heteroaryl group (preferably having 4 to 12 carbon atoms), and mayhave a substituent selected from the above-described Substituent GroupA. Further, a plurality of R^(A)'s may be the same as or different fromeach other. R^(A) is preferably a hydrogen atom or an alkyl group, andmore preferably a hydrogen atom.

L^(O1) represents any of a divalent to hexavalent linking groupincluding an aryl ring (preferably having 6 to 30 carbon atoms) or aheteroaryl ring (preferably having 4 to 12 carbon atoms). L^(O1) ispreferably an arylene group, a heteroarylene group, an aryltriyl group,or a heteroaryltriyl group, more preferably a phenylene group, abiphenylene group, or a benzenetriyl group, and still more preferably abiphenylene group or a benzenetriyl group. L^(O1) may have a substituentselected from the above-described Substituent Group A, and in a case ofhaving the substituent, the substituent is preferably an alkyl group, anaryl group, or a cyano group. Specific examples of L^(O1) include thefollowing.

n^(O1) represents an integer of 2 to 6, preferably an integer of 2 to 4,and more preferably 2 or 3. n^(O1) is most preferably 3 from theviewpoint of the efficiency of an element, or most preferably 2 from theviewpoint of the durability of an element.

The glass transition temperature (Tg) of the compound represented by thegeneral formula (O-1) is preferably from 100° C. to 300° C., morepreferably from 120° C. to 300° C., and still more preferably from 140°C. to 300° C., from the viewpoint of stability at the time of storage ata high temperature, or stable operation during driving at a hightemperature or against heat generation during driving.

Specific examples of the compound represented by the general formula(O-1) are shown below, but the compound represented by the generalformula (O-1), which can be used in the present invention, should not beconstrued to be limited to the specific examples.

The compound represented by the general formula (O-1) can be synthesizedby the method described in JP-A-2001-335776. After the synthesis,purification is preferably carried out by column chromatography,recrystallization, reprecipitation, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, moisture, or the likecan be removed effectively.

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (O-1) is preferably includedin the organic layer between the light emitting layer and the cathode,however, it is more preferably included in the layer on the cathode sideadjacent to the light emitting layer.

The compound represented by the general formula (O-1) is preferablycontained in the amount of 70% by mass to 100% by mass, and morepreferably 85% by mass to 100% by mass, with respect to the total massof the organic layer added.

The organic electroluminescent element of the present inventionpreferably includes at least one layer of organic layers between thelight emitting layer and the cathode, and it is preferable that theorganic layer contain at least one of compounds represented by thefollowing general formula (P), from the viewpoint of efficiency or thedriving voltage of an element. Hereinafter, the general formula (P) willbe described.

(In the general formula (P), R^(P) represents an alkyl group (preferablyhaving 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbonatoms), which may have a substituent selected from the above-describedSubstituent Group A. nP represents an integer of 1 to 10, and in thecase where there are a plurality of R^(P)'s, these may be the same as ordifferent from each other. At least one of R^(P)'s is a substituentrepresented by the following general formulae (P-1) to (P-3).

(In the general formulae (P-1) to (P-3), R^(P1) to R^(P3) and R′^(P1) toR′^(P3) each represent an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave a substituent selected from the above-described Substituent GroupA. n^(P1) and n^(P2) represent an integer of 0 to 4, and in the casewhere there are a plurality of R^(P1) to R^(P3) and R′^(P1) to R′^(P3),these may be the same as or different from each other. L^(P1) to L^(P3)represent any one of divalent linking groups consisting of a singlebond, an aryl ring, or a heteroaryl ring. * represents a bindingposition with the anthracene ring of the general formula (P)).

A preferred substituent other than the substituents represented by (P-1)to (P-3) as R^(P) is an aryl group, more preferably any one of a phenylgroup, a biphenyl group, a terphenyl group, and a naphthyl group, andstill more preferably a naphthyl group.

R^(P1) to R^(P3) and R′^(P1) to R′^(P3) are preferably any one of anaryl group and a heteroaryl group, more preferably an aryl group, stillmore preferably any one of a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, and most preferably a phenyl group.

L^(P1) to L^(P3) are preferably any one of divalent linking groupsconsisting of a single bond and an aryl ring, more preferably any one ofa single bond, phenylene, biphenylene, terphenylene, and naphthylene,and still more preferably any one of a single bond, phenylene, andnaphthylene.

Specific examples of the compound represented by the general formula (P)are shown below, but the compound represented by the general formula (P)that can be used in the present invention should not be construed to belimited to the specific examples.

The compound represented by the general formula (P) can be synthesizedby the method described in WO 2003/060956 and WO 2004/080975. After thesynthesis, purification is preferably carried out by columnchromatography, recrystallization, reprecipitation, or the like, andthen by sublimation purification. By the sublimation purification,organic impurities can be separated and inorganic salts, residualsolvents, moisture, or the like can be removed effectively.

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (P) is preferably includedin the organic layer between the light emitting layer and the cathode,and more preferably in the layer adjacent to the cathode.

The compound represented by the general formula (P) is preferablycontained in the amount of 70% by mass to 100% by mass, and morepreferably 85% by mass to 100% by mass, based on the total mass of theorganic layer added.

<Protective Layer>

In the present invention, the entirety of the organic electroluminescentelement may be protected by a protective layer.

For the protective layer, the detailed description in paragraph Nos.[0169] to [0170] of JP-A-2008-270736 can also be applied to the presentinvention. Incidentally, the materials for the protective layer may beeither an inorganic material or an organic material.

<Sealing Enclosure>

For the organic electroluminescent element according to the presentinvention, the entirety of the element may be sealed using a sealingenclosure.

For the sealing enclosure, the detailed description in paragraph No.[0171] of JP-A-2008-270736 can be applied to the present invention.

<Driving Method>

The organic electroluminescent element of the present invention can emitlight by applying a direct current (it may contain an alternate currentcomponent, if necessary) voltage (typically from 2 volts to 15 volts) ora direct current between the anode and the cathode.

As a driving method of the organic electroluminescent element of thepresent invention, driving methods described in JP-A-2-148687,JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234685, andJP-A-8-241047, Japanese Patent No. 2784615, and U.S. Pat. Nos. 5,828,429and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescentelement of the present invention is preferably 5% or more, morepreferably 6% or more, and still more preferably 7% or more. As to thenumerical value of the external quantum efficiency, a maximum value ofthe external quantum efficiency obtained when the organicelectroluminescent element is driven at 20° C., or a value of theexternal quantum efficiency in the vicinity of 300 cd/m² to 400 cd/m²obtained when the element is driven at 20° C. can be employed.

The internal quantum efficiency of the organic electroluminescentelement of the present invention is preferably 30% or more, morepreferably 50% or more, and still more preferably 70% or more. Theinternal quantum efficiency of the element is calculated by dividing theexternal quantum efficiency by the light extraction efficiency. Thelight extraction efficiency in usual organic EL elements is about 20%,but by taking into consideration the shape of a substrate, the shape ofan electrode, the thickness of an organic layer, the thickness of aninorganic layer, the refractive index of an organic layer, therefractive index of an inorganic layer, or the like, it is possible toincrease the light extraction efficiency to 20% or more.

<Light Emitting Wavelength>

In the organic electroluminescent element of the present invention, itslight emitting wavelength is not limited, but is preferably used forblue or white light emission. Above all, in the organicelectroluminescent element of the present invention, it is preferable touse the compound represented by the general formula (I) as a lightemitting material to emit light, and particularly preferably to emitblue light.

<Use of Organic Electroluminescent Element of the Present Invention>

The organic electroluminescent element of the present invention can besuitably used for display elements, displays, backlights,electrophotography, illumination light sources, recording light sources,exposure light sources, readout light sources, signs, billboards,interior decorations, optical communications, and the like, andparticularly preferably for devices driven in a region of high-intensityluminescence, such as a light emitting device, an illumination device,and a display device.

[Light Emitting Device]

The light emitting device of the present invention may include theorganic electroluminescent element of the present invention.

Next, the light emitting device of the present invention will bedescribed with reference to FIG. 2.

The light emitting device of the present invention is formed by usingthe organic electroluminescent element.

FIG. 2 is a cross-sectional view schematically showing one example ofthe light emitting device of the present invention. The light emittingdevice 20 in FIG. 2 includes a transparent substrate 2 (supportingsubstrate), an organic electroluminescent element 10, a sealingenclosure 16, and the like.

The organic electroluminescent element 10 is formed by laminating on thesubstrate 2 an anode 3 (first electrode), an organic layer 11, and acathode 9 (second electrode) in this order. In addition, a protectivelayer 12 is laminated on the cathode 9, and a sealing enclosure 16 isfurther provided via an adhesive layer 14 on the protective layer 12.Incidentally, a part of each of the electrodes 3 and 9, a diaphragm, aninsulating layer, and the like are omitted in FIG. 2.

Here, a photocurable adhesive such as an epoxy resin, or a thermosettingadhesive can be used for the adhesive layer 14, and for example, athermosetting adhesive sheet may also be used as the adhesive layer 14.

The light emitting device of the present invention is not particularlylimited in its use, and it can be used as not only an illuminationdevice but also a display device of a television set, a personalcomputer, a mobile phone, electronic paper, or the like.

[Illumination Device]

The illumination device of the present invention includes the organicelectroluminescent element of the present invention.

Next, the illumination device of the present invention will be describedwith reference to FIG. 3.

FIG. 3 is a cross-sectional view schematically showing one example ofthe illumination device of the present invention. The illuminationdevice 40 of the present invention includes, as shown in FIG. 3, theabove-described organic EL element 10 and a light scattering member 30.More specifically, the illumination device 40 is configured such thatthe substrate 2 of the organic EL element 10 and the light scatteringmember 30 are in contact with each other.

The light scattering member 30 is not particularly limited as long as itcan scatter light, but in FIG. 3, a member obtained by dispersing fineparticles 32 in a transparent substrate 31 is used. Suitable examples ofthe transparent substrate 31 include a glass substrate, and suitableexamples of the fine particles 32 include transparent resin fineparticles. As the glass substrate and the transparent resin fineparticles, a known product can be used for both. In such an illuminationdevice 40, when light emitted from the organic electroluminescentelement 10 is incident on the light incident surface 30A of thescattering member 30, the incident light is scattered by the lightscattering member 30 and the scattered light is output as illuminatinglight from the light output surface 30B.

[Display Device]

The display device of the present invention may include the organicelectroluminescent element of the present invention.

The display device of the present invention may be used for, forexample, a display device of a television set, a personal computer, amobile phone, electronic paper, or the like.

EXAMPLES

The characteristic features of the present invention are hereunderdescribed in more detail with reference to the following Examples andComparative Examples. The materials, use amounts, ratios, treatmentdetails, treatment procedures, and the like shown in the followingExamples and Comparative Examples can be appropriately modified so faras the gist of the present invention is not deviated. Accordingly, itshould not be construed that the scope of the present invention islimited to the specific examples shown below.

Example 1 Synthesis of Compound 1

A compound 1 was synthesized according to the following scheme.

Compounds 1 to 5 used in Examples as well as the compounds other thanthe compound 1 synthesized above were synthesized by a method similar tothat for the compound 1. Comparative compounds D1 and D2 weresynthesized with reference to US2008-0100208 A1.

The structural formulae of the compounds 1 to 5 represented by thegeneral formula (I) used in Examples, and the structural formulae of thecompounds D1 and D2 used in Comparative Examples are summarized below.

The following comparative compounds D1 and D2 are the compoundsdescribed in US2008-0100208 A1.

The materials other than the compounds 1 to 5 of the present inventionand the comparative compounds D1 and D2, which were used in the case offabrication of organic electroluminescent elements are shown below.

Example 2 Organic Electroluminescent Elements 1 to 5 of the PresentInvention, and Comparative Elements 1 and 2

(1) Purity of Materials Used

The materials used for fabrication of the elements were all subjected tosublimation purification and it was confirmed that the purity(absorption intensity area ratio at 254 nm) was 99.0% or more by usinghigh performance liquid chromatography (TSKgel ODS-100Z, manufactured byTosoh Corporation).

(2) Fabrication of Elements

A 0.5 mm-thick and 2.5 cm square glass substrate (manufactured byGeomatec Co., Ltd., surface resistance: 10Ω/□) having an ITO filmthereon was put in a cleaning container. After ultrasonic cleaning in2-propanol, the glass substrate was subjected to a UV-ozone treatmentfor 30 minutes. The following organic compound layers were depositedsequentially on this transparent anode (ITO film) by a vacuum depositionmethod. The film thickness was monitored by a quartz crystal oscillator.

First layer (hole injecting layer): CuPc: Film thickness 10 nm (filmforming rate: 1 angstrom/s)

Second layer (hole transporting layer): NPD: Film thickness 30 nm (filmforming rate: 1 angstrom/s)

Third layer (light emitting layer): Host material ADN and the lightemitting material descried in Table 1 below (mass ratio=95:5): Filmthickness 40 nm (film forming rate: 0.1 angstroms/s, 1 angstrom/s, or 5angstroms/s)

Fourth layer (electron transporting layer): Alq: Film thickness 30 nm(film forming rate: 1 angstrom/s)

1 nm of lithium fluoride and 100 nm of metallic aluminum were depositedin this order thereon, thereby forming a cathode. Further, a patternedmask (mask having a light emitting area of 2 mm×2 mm) was provided onthe layer of lithium fluoride, and metallic aluminum was deposited.

The obtained laminate was put in a glove box purged with a nitrogen gaswithout bringing it into contact with the atmosphere and then sealedwith a sealing can made of glass and an ultraviolet ray-curable adhesive(XNR5516HV, manufactured by Nagase-CHIBA Ltd.), thereby obtaining theorganic electroluminescent elements 1 to 5 of the present invention, andcomparative elements 1 and 2.

(3) Evaluation of Elements

For the organic electroluminescent elements 1 to 5 of the presentinvention, and the comparative elements 1 and 2 obtained above, thefollowing evaluation was carried out. The results are shown in Table 1below.

(a) External Quantum Efficiency (Luminous Efficiency)

Light was emitted by applying a direct current voltage to an organicelectroluminescent element (fabricated under an environment of a dewpoint temperature of −60° C.) at a constant current intensity (25mA/cm²) by using a source measure unit 2400 manufactured by TOYOCorporation. The luminance was measured using a luminance meter BM-8manufactured by Topcon Corporation. The luminous spectrum and the lightemitting wavelength were measured using a spectrum analyzer PMA-11manufactured by Hamamatsu Photonics K. K. Based on these values, theexternal quantum efficiency was calculated by using a luminanceconversion method, and shown as a relative value, taking the value ofthe comparative element 1 when the film forming rate of the lightemitting layer was 1 angstrom/s as 1. A larger numeral value of theexternal quantum efficiency is more preferable.

(b) Driving Voltage

The organic electroluminescent element was set on a luminous spectrummeasurement system (ELS1500) manufactured by Shimadzu Corporation, andlight was emitted at a constant current intensity (25 mA/cm²). At thattime, the applied voltage was measured and shown as a relative value,taking the value of the comparative element 1 when the film forming rateof the light emitting layer was 1 angstrom/s as 10. A lower value of thedriving voltage is more preferable.

(c) Driving Durability

A direct current voltage was applied to an organic electroluminescentelement at a constant current intensity to give a luminance of 5000cd/m², thereby emitting light continuously at the current intensity, andthe time taken until the luminance became 2500 cd/m² was measured andshown as a relative value, taking the value of the comparative element 1when the film forming rate of the light emitting layer was 1 angstrom/sas 100. A larger numeral value indicates higher durability, which ispreferable.

TABLE 1 Light (a) External quantum efficiency (b) Driving voltage (c)Driving durability emitting 0.1 ang- 0.1 ang- 0.1 ang- 5 ang- materialstroms/s 1 angstroms/s 5 angstroms/s stroms/s 1 angstroms/s 5angstroms/s stroms/s 1 angstroms/s stroms/s Comparative D1 0.8 1 0.6 1110 13 75 100 80 element 1 Comparative D2 0.7 0.8 0.5 14 14 17 25 60 20element 2 Element 1 of the 1 1.5 1.5 1.4 9 9 9 110 120 100 presentinvention Element 2 of the 2 1.3 1.3 1.3 10 10 10 80 100 95 presentinvention Element 3 of the 3 1.0 1.1 1.0 10 10 10 100 115 100 presentinvention Element 4 of the 4 1.2 1.2 1.1 8 8 8 90 105 95 presentinvention Element 5 of the 5 0.9 1.0 0.8 10 10 10 90 110 100 presentinvention

As clearly seen from the results in Table 1 above, it could be confirmedthat the organic electroluminescent elements of the present inventionusing the compounds of the present invention exhibit stable performance,irrespective of the deposition rates of the light emitting layers, ascompared with the respective comparative elements using the compounds inthe related art. This is highly advantageous in that products exhibitingstable performance can be produced under various preparationenvironments and preparation conditions.

REFERENCE SIGNS LIST

-   -   2: SUBSTRATE    -   3: ANODE    -   4: HOLE INJECTING LAYER    -   5: HOLE TRANSPORTING LAYER    -   6: LIGHT EMITTING LAYER    -   7: HOLE BLOCKING LAYER    -   8: ELECTRON TRANSPORTING LAYER    -   9: CATHODE    -   10: ORGANIC ELECTROLUMINESCENT ELEMENT    -   11: ORGANIC LAYER    -   12: PROTECTIVE LAYER    -   14: ADHESIVE LAYER    -   16: SEALING ENCLOSURE    -   20: LIGHT EMITTING DEVICE    -   30: LIGHT SCATTERING MEMBER    -   31: TRANSPARENT SUBSTRATE    -   30A: LIGHT INCIDENT SURFACE    -   30B: LIGHT OUTPUTTING SURFACE    -   32: FINE PARTICLES    -   40: ILLUMINATION DEVICE

The invention claimed is:
 1. An organic electroluminescent elementcomprising: a substrate; a pair of electrodes including an anode and acathode, disposed on the substrate; and at least one organic layerincluding a light emitting layer, disposed between the electrodes,wherein at least one kind of compound represented by the followinggeneral formula (I) is contained in any layer of the at least oneorganic layer:

wherein L¹, L², L³ and L⁴ each independently represent a linking group;n¹, n², n³ and n⁴ represent 0 or 1, satisfying n¹+n²=1 and, n³+n⁴=1; A¹,A⁵, A⁶ and A¹⁰ each represent a C atom, C—R¹, or an N atom; and when n¹is 1, A¹ represents a C atom, when n² is 1, A⁵ represents a C atom, whenn³ is 1, A⁶ represents a C atom, when n⁴ is 1, A¹⁰ represents a C atom,when n¹ is 0, A¹ represents C—R¹ or an N atom, when n² is 0, A⁵represents C—R¹ or an N atom, when n³ is 0, A⁶ represents C—R¹ or an Natom, and when n⁴ is 0, A¹⁰ represents C—R¹ or an N atom; A², A³, A⁴,A⁷, A⁸ and A⁹ each independently represent C—R¹ or an N atom; R¹'s eachindependently represent a hydrogen atom or a substituent; represents asubstituent bonded to the pyrene skeleton and m represents 0 to 6;wherein when m is 2 or more, R's, which are present in plural, may bethe same as or different from each other, but there is no case where theadjacent R's are bonded to each other to form a ring.
 2. The organicelectroluminescent element according to claim 1, wherein in the generalformula (I), L¹, L², L³ and L⁴ are each independently CR¹²R¹³, NR¹⁴,SiR¹⁵R¹⁶, an O atom, or an S atom, wherein R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶each independently represent a fluorine atom, an alkyl group, an arylgroup, or a heteroaryl group.
 3. The organic electroluminescent elementaccording to claim 1, wherein the compound represented by the generalformula (I) is a compound represented by the following general formula(II):

wherein L¹ and L³ each independently represent a linking group; A², A³,A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ each independently represent C—R¹ or an Natom; R¹'s each independently represent a hydrogen atom or asubstituent; R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6; wherein when m is 2 or more, R's, which arepresent in plural, may be the same as or different from each other, butthere is no case where the adjacent R's are bonded to each other to forma ring.
 4. The organic electroluminescent element according to claim 3,wherein in the general formula (II), L¹ and L³ are each independentlyCR¹²R¹³NR¹⁴, SiR¹⁵R¹⁶ an O atom, or an S atom, wherein R¹², R¹³, R¹⁴,R¹⁵ and R¹⁶ each independently represent a fluorine atom, an alkylgroup, an aryl group, or a heteroaryl group.
 5. The organicelectroluminescent element according to claim 3, wherein in the generalformula (II), A², A³, A⁴, A⁵, A⁷, A⁸, A⁹ and A¹⁰ are each independentlyC—R¹.
 6. The organic electroluminescent element according to claim 1,wherein the compound represented by the general formula (I) is acompound represented by the following general formula (III):

in which L² and L⁴ each independently represent a linking group; A¹, A²,A³, A⁴, A⁶, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an Natom; R¹'s each independently represent a hydrogen atom or asubstituent; R represents a substituent bonded to the pyrene skeletonand m represents 0 to 6; when m is 2 or more, R's, which are present inplural, may be the same as or different from each other, but there is nocase where the adjacent R's are bonded to each other to form a ring. 7.The organic electroluminescent element according to claim 6, wherein inthe general formula (III), L² and L⁴ are each independently CR¹²R¹³,NR¹⁴, siR¹⁵R¹⁶, an O atom, or an S atom, wherein R¹², R¹³, R¹⁴, R¹⁵ andR¹⁶ each independently represents a fluorine atom, an alkyl group, anaryl group, or a heteroaryl group.
 8. The organic electroluminescentelement according to claim 6, wherein in the general formula (III), A¹,A², A³, A⁴, A⁶, A⁷, A⁸ and A⁹ are each independently C—R¹.
 9. Theorganic electroluminescent element according to claim 1, wherein thecompound represented by the general formula (I) is contained in thelight emitting layer.
 10. The organic electroluminescent elementaccording to claim 1, wherein the compound represented by the generalformula (I) is a light emitting material contained in the light emittinglayer.
 11. The organic electroluminescent element according to claim 10,further comprising a host material in the light emitting layer.
 12. Theorganic electroluminescent element according to claim 11, wherein thehost material has an anthracene skeleton.
 13. The organicelectroluminescent element according to claim 1, wherein the organiclayer containing the compound represented by the general formula (I) isformed by a vacuum deposition process.
 14. A light emitting devicecomprising the organic electroluminescent element according to claim 1.15. A display device comprising the organic electroluminescent elementaccording to claim
 1. 16. An illumination device comprising the organicelectroluminescent element according to claim
 1. 17. A compoundrepresented by the following general formula (I):

wherein L¹, L², L³ and L⁴ each independently represent a linking group,n¹, n², n³ and n⁴ represent 0 or 1, with the proviso that when n¹ and n³are each 1, then L¹ and L³ cannot both be S, satisfying n¹+n²=1 andn³+n⁴=1; A¹, A⁵, A⁶ and A¹⁰ each represent a C atom, C—R¹ or an N atom;and when n¹ is 1, A¹ represents a C atom, when n² is 1, A⁵ represents aC atom, when n³ is 1, A⁶ represents a C atom, when n⁴ is 1, A¹⁰represents a C atom, when n¹ is 0, A¹ represents C—R¹ or an N atom, whenn² is 0, A⁵ represents C—R¹ or an N atom, when n³ is 0, A⁶ representsC—R¹ or an N atom, when n⁴ is 0, A¹⁰ represents C—R¹ or an N atom; A²,A³, A⁴, A⁷, A⁸ and A⁹ each independently represent C—R¹ or an N atom;R¹'s each independently represent a hydrogen atom or a substituent; Rrepresents a substituent bonded to the pyrene skeleton and m represents0 to 6; wherein when m is 2 or more, R's, which are present in plural,may be the same as or different from each other, but there is no casewhere the adjacent R's are bonded to each other to form a ring.